of chicago



Patented Mar. 15, 1927.

UNITED STATES PATENT OFFICE.

ERNEST H. VOLWILEB, OF CHICAGO, ILLINOIS, ASSIGNOB TO ABBOTT LABORATORIES,

OF CHICAGO, ILLINOIS, A CORPORATION OF TLLINOIS.

N-BUTYL ETHYL BARBITURIC SUBSTANCE.

1T0 Drawing. Application filed July 18,

My invention relates to the production of n-butyl ethyl barbituric substances wh1ch are of particular value as hypnotics.

These new hypnotic compounds may be 5 represented by the formula:

where, in the case of the acid, X represents h drogen, or in the case of the organlc. salt )3 represents H plus the organic basic radical, or in the case of the inorganic salts X represents the inorganic bas1c radical, for example, a metal. I

The organic salts are represented by the formula:

(1004B 0--NH i\o/C eo (411/ \C0--NHY/ where Y is an organic basic radical.

These new compounds possess remarkable as hypnotic action, producing sleep in small doses and having a relatively low toxleity. The acid, n-butyl-ethyl barb1tur1c and, maybe produced by any of the ordinary methods for preparing 5, 5-disubst1tuted barbituric acids. For example, 107 grams n-butyl-ethyl malonic ethyl-ester and 38 grams urea are added to a solution of 30.1

grams sodium in 567 grams absolute alcohol,

and heated in an autoclave at 105 for five hours. The alcohol is then distilled oil, the 5 residue taken up in water, and acidified with a mineral acid, whereupon thevcrude n-butyl-ethyl barbituric acid separates out. Upon recrystallization from dilute alcohol, it exists as a white solid, melting at 126- 40 127 C. It is very slightly soluble in water, but readily soluble in alcohol, ether, etc.

The organic salts may be prepared by treating the acid with the organic base and warming, whereupon the salt is readily formed and on cooling usually crystallizes from the solution. In many cases the salt is soluble in water.

Speez'fia examples of the organic salts.

1923. Serial No. 652,454.

ine. 21.6 grams of n-butyl-ethyl-barbituric cooling the product crystallizes. After allowing the excess amine to evaporate ofl',

the material melts at about C. It is readily soluble in water and alcohol, less so in ether, and insoluble in ligroin.

n-butyl-ethyl-barbiturate of di-n-butyl amine. 21.2 grams of n-butyl-et-hyl-barbituric acid are warmed with 15 grams di-nbutyl amine to C. for an hour. After removing the excess di-n-butyl amine by warming in vacuo, the crystalline solid obtained on cooling melts at about 70 C. It is only slightl soluble 'in water, but more soluble in alco ol.

Ammonium. n-butyl ethyl barbiturate. The ammonium saltof n-butyl-ethyl-barbituric acid may be prepared in solution by dissolvin the n-butyl-ethyl barbituric acid in a slig t excess of concentrated aqueous ammonia solution.

The inorgam'o salts.

termined by reference to the appended claim,

said claim being construed as broadly as possible, consistent with the state of the art.

I claim as my invention:

The new hypnotic substance" formed by the reaction of n-butyl-ethyl barbituric acid with diethyl-amine, which is a white solid, melting at'about 60 (1, being soluble in water and having an ammonia-like and slightly bitter taste.

ERNEST H. VOLWILER. 

